House vacation rentals in Middletown

Find and book unique houses on Airbnb

Top-rated house rentals in Middletown

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in La Grange

5 out of 5 average rating, 238 reviews

Your Cozy Get Away Cabin with Hot Tub

This cabin is a completely renovated 1940's farm house 10 minutes from historic downtown LaGrange. Guests have the entire home with front and back porch overlooking the big backyard. The master bedroom has a queen bed and the second bedroom has a full bed. The kitchen is fully equipped and ready for some country cooking. The fire pit is located in the back yard ready for you or you can use the gas fire pit just steps from the hot tub. The hot tub is ready for guests with a view of stars!

Guest favorite

Home in Elizabeth

4.86 out of 5 average rating, 182 reviews

Relaxing River House Retreat-Sleeps 10-12

Cozy newly renovated river house with ample entertainment space inside and out. Large covered deck with wrap around porch and a beautiful view of the Ohio River. 1 mile from Horseshoe Casino, just minutes from entertainment and amenities of downtown New Albany, IN and Louisville, KY. Less than 10 minutes from a local winery, 2 breweries, and Chariot Run Golf Course. Perfect for large groups or a romantic weekend getaway! Additional detached bonus bedroom. $100 extra per stay at guest's request.

Superhost

Home in Louisville

4.87 out of 5 average rating, 333 reviews

Designed for Families • Peaceful Neighborhood

Perfect for Families - We love hosting families! We have a little kids, so we know how nice it is to stay in a home with essentials for the littles. The kids’ room includes a pack 'n play, highchair, chalkboard wall, and a variety of books and toys. Enjoy family movie time with Disney+. Safe & Central Location – Situated in a quiet, centrally located neighborhood with easy access to top attractions, all within a 10-minute drive. We're Legally Registered - illegal listings may be shut down.

Top guest favorite

Home in Louisville

4.95 out of 5 average rating, 171 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Guest favorite

Home in Louisville

4.87 out of 5 average rating, 171 reviews

Prime Highlands Location - 500ft fro. Midcity Mall

Formerly known as Breslin House, this well-loved Airbnb (126 five stars reviews) is under a new host. We are confident you'll love it as much as everyone did before! Our house is located on a quiet street, but steps away from restaurants, bars, boutiques, and cafes on Bardstown Rd. It's perfectly situated in the heart of the Highlands so you can walk to almost everywhere. Our home is very spacious with 3 large bedrooms, so you'll have plenty of privacy even with a large group.

Guest favorite

Home in Louisville

4.96 out of 5 average rating, 223 reviews

502 House @ Progress Park w/ Game Room

Welcome to Progress Park! A true getaway for fun! Located on a 12 acre Airstream Glamping resort w/ a 2 acre swimming pond. Sleeps 8 comfortably in the beds with 2 leather futons. Enjoy all the luxuries of home w/ added amenities such as a custom game room & luxurious backyard with TV, firepit & grill. Relax, unplug and reconnect in our little slice of heaven. Progress Park has 8 total units on site. 2 houses, 5 airstreams & a bunk house. *DERBY IS A MIN THURS-SUN REQUIRED

Guest favorite

Home in Highlands

4.92 out of 5 average rating, 214 reviews

Walk to All! 2 Kings, 2.5 baths, washer/dryer

3 story townhouse in city's best location. 1/2 block to great restaurants, cafes, shops and Cave Hill. Parking for 2 cars. Sleeps 8 in two king bedrooms and 2 sleeper sofas. 3 bathrooms (2 full and a 1/2) Wifi, gas fireplace, cable, lux linens, washer/dryer (with detergent/dryer sheets), fully equipped kitchen and more! Great local coffee just across street. Two of Louisville's best restaurants with 2 blocks. Half dozen fun nightspots within a 2 minute walk.

Guest favorite

Home in New Albany

4.95 out of 5 average rating, 209 reviews

The Green House in Downtown

Newly renovated 1920s shotgun house in Downtown New albany. Perfect for those who want the convenience of being in the middle of it all, but still want an authentic and stylish oasis to relax in. Comes with all the amenities you would expect for a convenient stay including fully equipped kitchen, private back yard, off street parking, and self check-in. Walk or Bike your way to many local restaurants, shops, or take the byway to enjoy the scenic Ohio River.

Guest favorite

Home in Louisville

4.91 out of 5 average rating, 156 reviews

New Signature Highlands Home- steps away from…

Welcome to our new to AirBNB Highlands home. Recently redecorated and updated, this home is steps away from many incredible local restaurants, bars, and shops. Less then one mile to Cherokee Park. Less then five miles to Churchill Downs, NULU, and the airport. You simply can’t beat this location. Safe, family friendly neighborhood with swing-set in the back yard (high chair, pack and play, toys, and more available upon request).

Guest favorite

Home in Germantown

4.94 out of 5 average rating, 120 reviews

Spruced-Up Shotgun, Steps to Logan St Market

Recently renovated full 2 bed/2 bath house in historic Germantown. Guest will enjoy a full kitchen with all utensils and appliances provided. Living room has 55' TV with plenty seating and light. Each bedroom has double bed with linens, dressers, nightstand, and closet. Full bathroom connected to each bedroom with towels and toiletries. Front and back door uses coded Yale locks. Security cameras on front and back doors.

Guest favorite

Home in New Albany

4.94 out of 5 average rating, 143 reviews

king bed and oasis backyard with hot tub

11 miles to Derby. Come enjoy our newly decorated house with a hot tub, gazebo outdoor fun area and lounge furniture and wood burning fire pit. The idea is to both indoor and outdoor give you a great experience that not everyone offers! We sleep 4 adults comfortably in our 1 KING size bedroom and 1 QUEEN size bedroom. We're located in a quiet neighborhood with a fully fenced in backyard and we're Pet Friendly with a fee!

Top guest favorite

Home in East Market District

5 out of 5 average rating, 138 reviews

Walkable+5 King Beds+Firepit+Bourbon Trail

Welcome to Washington Landing! From here, you will be perfectly poised to enjoy all the shops, breweries, restaurants, distilleries, waterfront concerts and the professional soccer stadium all within WALKING DISTANCE of this newly remodeled 4 bed/2 bath historic home. You would be hard pressed to find a better location! No locals No Parties - only registered guests

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What guests are saying

Bourbon by the Lake

5 out of 5 average rating, 23 reviews2 weeks ago

This is the second time we’ve stayed at Emily’s house. It is just perfect for our “girl trip”! We enjoyed shopping at the outlets, and going to the lavender farm. The house is spotless, linens are freshly laundered!! The location is so beautiful and peaceful. And what makes it “perfect” is Emily’s kindness and responsiveness. Will definitely go again!!

Home in Shelbyville

What guests are saying

Historic Triple Crown House - Fully Renovated

4.79 out of 5 average rating, 113 reviews1 week ago

Beautiful place and great location! 15 minutes from the airport and 10-15 minutes to downtown Louisville. Grocery store is 2 minutes away which made it very easy to get the essentials. Had all the amenities listed and nice seating area in the front and back of the house. Would highly recommend this place! Jeff was very responsive and easy to talk to!

Home in Louisville

What guests are saying

Bourbon Trail Bungalow with Hot Tub and play park!

5 out of 5 average rating, 20 reviews1 week ago

Everything about this place is PERFECT. Upon opening the door, the smell of clean was amazing!!!!! Just from opening the door I just knew it was the right stay for two family's while at a Volleyball tournament at the Expo Center. The beds are comfy. The linens were clean and soft! The host were great! The host made you feel right at home, they had some fresh fruit, a box of Capri suns, few pops and waters and a bowl of snacks! The hot tub was clean and amazing! Fans in every room, the fridge has an ice machine and good tasting water. The host left laundry soap, dish washer soap and extra towels if needed, even for the hot tub! The yard was taken care of and nicely mowed. This place was decorated so cute!!!! Someone really took some time! The drive to the Expo center was about 20 mins wasn't bad at all! I really cant tell you enough how much we enjoyed our stay in this home. We will be back next year!!!!!!!

Home in Mount Washington

What guests are saying

Sleek Urban Getaway Paristown/Highland/Germantown

4.95 out of 5 average rating, 42 reviews2 weeks ago

Alan’s was great for us even with kids. Has stairs but easy enough for my 2 and 4 year old! House was clean and spacious! Hot tub was also great! Only took us minutes to go anywhere we wanted. The Louisville zoo was super close and a great time with the littles. Would definitely stay again. Alan was easy to reach and had great suggestions!

Home in Germantown